I'm thinking about some times when I chose "paid" over "free" and a big part of it was that the paid option was 1) considerably better and 2) unavailable for free due to physical limitations.

The first example I thought of was when I was younger and wanted internet access. I didn't pay for dialup as long as I could figure out a free option. Our library had some free system you could dial into and I figured out a way to make reasonable use of that. Then when I moved, I used some of those Juno and Netzero type services for a while.

But once I had the option to pay for cable internet, I just went straight for it. The experience was an order of magnitude better, and there was simply no way to hustle a roughly equivalent free option out there. But looking back, I don't know if I would've considered a free, ad-based cable provider if it existed back when I was a broke young dude pinching pennies wherever I could.

Then again, nowadays, I would pay a bit extra to ensure my cable internet provider did not read, prioritize, or otherwise mess with my data if that was an option. But I doubt many others would choose to do that if it was extra charge for nebulous benefits.

I would say that there's two models driving us to hell. In addition to the ad-supported model, there's also the "everything is a service" model. The AAS model is increasingly the only alternative to the ad-supported model that's available to those of us willing to pay for nice things. Teslas and iPhones are certainly not free, yet they're just as much inscrutable black-boxes as low-end smartphones and commodity "smart" TVs. The only difference is that they spend less time misbehaving because of careless updates, since this model motivates the manufacturers to invest more in QA. They're less openly hostile-seeming because they view the user like a high-end hotel views a guest - to be pampered and indulged. But the "user" is still a guest with limited-time and carefully-controlled access to the facilities, not an owner.